Manufacturer: Hangzhou Royalchem Co.,LTD.
Website: www.cnroyalchem.com
1. Chemical Identification & Structure
Product Name: Benzyl (4-Fluorophenyl)carbamate
Common Synonyms:
N-(4-Fluorophenyl)carbamic Acid Benzyl Ester
Carbamic Acid, N-(4-Fluorophenyl)-, Phenylmethyl Ester
Benzyl N-(p-Fluorophenyl)carbamate
Benzyl 4-Fluorophenylcarbamate
Benzyl (p-Fluorophenyl)carbamate
CAS Registry Number: 149524-47-0
Molecular Formula: C₁₄H₁₂FNO₂
Molecular Weight: 245.25 g/mol
Chemical Structure: O=C(OCc1ccccc1)NC2=CC=C(F)C=C2
Core Structure: Carbamate group (-NH-C(=O)-O-)
Substituents: 4-Fluorophenyl group attached to the nitrogen (N), Benzyl group (C₆H₅CH₂-) attached to the carbonyl oxygen (O).
Isomer: Specifically the para -isomer (4-fluorophenyl).
2. Physical and Chemical Properties
Appearance: Typically a white to off-white crystalline solid or powder.
Melting Point: Approximately 119-123 °C (literature value, may vary slightly by batch/purity).
Solubility:
Soluble in: Common organic solvents like Dichloromethane (DCM), Chloroform (CHCl₃), Ethyl Acetate (EtOAc), Dimethylformamide (DMF), Dimethyl Sulfoxide (DMSO), Acetonitrile (MeCN).
Sparingly soluble or Insoluble in: Water, Hexane, Petroleum Ether.
Storage Conditions:
Store in a cool (2-8°C recommended), dry place.
Keep container tightly sealed under an inert atmosphere (e.g., nitrogen or argon) to minimize moisture absorption and potential decomposition.
Store away from light, heat, strong oxidizing agents, and strong bases.
Stability: Stable under recommended storage conditions. May decompose upon prolonged exposure to moisture, strong acids, strong bases, or high temperatures. Carbamates can hydrolyze.
3. Primary Applications & Uses
Protecting Group Reagent: Its primary use in organic synthesis is as a protecting group for amines , specifically for aniline derivatives. The benzyl carbamate group (Cbz or Z group) introduced by this reagent protects the amine functionality (-NH₂) during multi-step synthesis.
Protection: Reacts with aromatic amines (like 4-fluoroaniline) under standard conditions (e.g., in the presence of a base like pyridine or triethylamine, potentially with activating agents like DMAP) to form the stable Cbz-protected amine ( N-Cbz-4-fluoroaniline ).
Deprotection: The protecting group can be selectively removed later under mild conditions, commonly via catalytic hydrogenation (H₂, Pd/C catalyst) or acidic conditions (e.g., HBr in acetic acid, TMSI), regenerating the free amine without affecting many other functional groups.
Building Block/Intermediate: Serves as a versatile synthetic intermediate for preparing more complex molecules, particularly in:
Pharmaceutical research (development of drug candidates).
Agrochemical research.
Material science.
Synthesis of peptides (less common for aromatic amines, but applicable).
Synthesis of functionalized ureas or other carbamate derivatives.
4. Safety Information (GHS - Example - Consult SDS for Specific Product)
Hazard Statements (H-Statements - Typical):
H315: Causes skin irritation.
H319: Causes serious eye irritation.
H335: May cause respiratory irritation.
H302: Harmful if swallowed.
Precautionary Statements (P-Statements - Typical):
P261: Avoid breathing dust/fume/gas/mist/vapours/spray.
P264: Wash skin thoroughly after handling.
P270: Do not eat, drink or smoke when using this product.
P271: Use only outdoors or in a well-ventilated area.
P280: Wear protective gloves/protective clothing/eye protection/face protection.
P301 + P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
P302 + P352: IF ON SKIN: Wash with plenty of soap and water.
P305 + P351 + P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P332 + P313: If skin irritation occurs: Get medical advice/attention.
P337 + P313: If eye irritation persists: Get medical advice/attention.
P362 + P364: Take off contaminated clothing and wash it before reuse.
P403 + P233: Store in a well-ventilated place. Keep container tightly closed.
P405: Store locked up.
Handling Precautions:
Handle in a well-ventilated fume hood.
Wear appropriate personal protective equipment (PPE): Safety glasses or goggles, chemical-resistant gloves (e.g., nitrile, neoprene), lab coat.
Avoid contact with skin, eyes, and clothing. Avoid inhalation of dust.
Use non-sparking tools. Ground containers during transfer.
First Aid Measures:
Inhalation: Move to fresh air. If breathing is difficult, give oxygen. Seek medical attention.
Skin Contact: Remove contaminated clothing. Wash skin thoroughly with soap and water. Seek medical attention if irritation develops.
Eye Contact: Rinse cautiously with water for at least 15 minutes, lifting upper and lower eyelids. Seek immediate medical attention.
Ingestion: Rinse mouth. Do NOT induce vomiting. Seek immediate medical attention.
